Schttlemann



Patented Feb; 1a, 1930] UNITED STATES} PATENT OFFICE GERMANY, ASSIGNORSTO .WINTHROP v CHEMICAL COMPANY, INC., OF

YORK, N. Y.

NEW

'NEW G-ALKOXY-S-AMIN O QUINOLINES No Drawing. Original application filedJanuary 30, 1926, Serial-No. 85,080, and in Germany April 29,

1925. Divided and this application filed May 16, 1928, Serial No.278,831. I

The present invention concerns the hitherto unknown6-alkolxy-S-amino-quinolines and in particular the6-methoxy-8-amioquinoline, which substances exhibit antipyreticproperties similar to those of the 5-amino-8-ethoxy-quinoline, and alsoexert-a strong specific destroying action on blood. parasites.

This is a division of our application Serial 10 No. 85,030, filed onJanuary 30, 1926.

These compounds are obtained by the reduction of6-alkoxy-8-nitro-quinolines or from 6-alkoxy-8-azoaryl-quinolinesaccording to the methods ordinarily used for the reduction of thesecompounds.

The 6-alkoxy-8-amino-quinolines are intended to find application ascurative products and to serve as intermediates for the manufacture ofderivatives which are of value in pharmacy.

The following example will serve to illustrate our invention.

Example:

5 kilos of 6-methoxy-8-nitro:quinoline are dissolved in 20 litres ofpure concentrated hydrochloric acid of about strength, the solution isheated to 100 (3., and poured while at this temperature into 60 litresof a containing 600 stannous chloride solution,

grams of stannous chloride per heating for one hour to 100 C 100 litresof concentrated hydrochloric acid of 35% are added, when after coolingthe stannous chloride double salts separates; this is filteredoif,washed with hydrochloric acid of 30%, and decomposed in thecustomary manner.

The resulting 6-methoxy-8-amino-quinoline distills at 137-138 O. at apressure of about 1 mm. of mercury. It forms a viscous, light yellowoil, which solidifies to an almost white crystalline mass havin amelting point of 41 C. With hydroch orio acid it forms a beautifullycrystalline inonohydrochloride,

- at about 41 C., I hydrochloric acid,

litre. After possessing an orange color and which dissolves in coldwater with difiiculty. Instead of stannous chloride other reducingagents such as zincor iron can be used, or electrolytic reduct onmayalso, be resorted to.

In general the present invention comprises reducing 6-alkoxy-quinolinecompounds havlng in the 8-position a nitrogen-containing group capableof conversion into the amino group by reduction, such .as the nitroorthe arylazo-groups, by means of the known reduction procedures.

We claim: i

The hereindescribed new 6-methoxy-8- ammo-quinoline having most probablythe following formula:

being a whitish crystalline substance melting forming soluble salts withproperties and exerting a strong specific destroying action on bloodparasites.

In testimony whereof, we aflix our signatures.

WERNER S( HUL EMANN. FRITZ SCHONHOFER. FRITZ MIETZSCH.

exhibiting antipyretio

